160.Total Syntheses of Vicinal Dichloride Monoterpenes Enabled by AzaBellus−̌ Claisen Rearrangement

Jiangqun Cheng, Yuan-He Li, Jun Huang,* and Zhen Yang*

Org. Lett. 2021, 23(21), 8465–8470

Diastereoselective syntheses of syn– and anti-vicinal dihalides were achieved via an aza-Belluš–Claisen rearrangement, which involved the reaction of an α-chloro carboxylic acid chloride with halogen-substituted trans-allyl morpholines in the presence of Lewis acids. The developed method was used for the total synthesis of a group of monoterpene natural products bearing vicinal dichloride subunits.